Liquid shortening containing brassidoyl propylene glycol hydrogen succinate

ABSTRACT

THE NOVEL COMPOUND BRASSIDOYL PROPYLENE GLYCOL HYDROGEN SUCCINATE (BSPGHS) HAVING USE AS A SHORTENING COMPOSITION ADDITIVE IS PRODUCED. A NOVEL LIQUID SHORTENING COMPOSITION IS ALSO PRODUCED BY MIXING A GLYCERIDE BASE OIL, BSPGHS, PROPYLENE GLYCOL FATTY MONOESTER AND MONO- AND DIGLYCERIDES, DESMOKING THE MIXTURE AND WINTERIZING THE DESMOKED MIXTURE. THE SHORTENING COMPOSITION IS CLEAR AT TEMPERATURE ABOVE 60*F., POURABLE AT REFRIGERATOR TEMPERATURES, RAPIDLY RECOVERS ITS CLARITY WHEN REMOVED FROM REFRIGERATOR TEMPERATURES TO TEMPERATURES ABOVE 60*F., HAS MINIMAL SMOKING TENDENCIES, AND POSSESSES EXCELLENT CAKE BAKING PROPERTIES.

United States Patent Office 3,694,215 Patented Sept. 26, 1972 LIQUIDSHORTENING CONTAINING BRASSIDOYL PROPYLENE GLYCOL HYDROGEN SUCCINATEPaul Seiden, Cincinnati, Ohio, assignor to The Procter & Gamble Company,Cincinnati, Ohio No Drawing. Filed Dec. 29, 1970, Ser. No. 102,525 Int.Cl. A23d 5/00 U.S. Cl. 99-118 F 8 Claims ABSTRACT OF THE DISCLOSURE Thenovel compound brassidoyl propylene glycol hydrogen succinate (BSPGHS)having use as a shortening composition additive is produced. A novelliquid shortening composition is also produced by mixing a glyceridebase oil, BSPGHS, propylene glycol fatty monoester and monoanddiglycerides, desmoking the mixture and winterizing the desmokedmixture. The shortening composition is clear at temperatures above 60F., pourable at refrigerator temperatures, rapidly recovers its claritywhen removed from refrigerator temperatures to temperatures above 60 F.,has minimal smoking tendencies, and possesses excellent cake bakingpoperties.

BACKGROUND OF THE INVENTION This invention relates to a novel compoundhaving utility as an additive for a novel shortening composition.Additionally, this invention relates to liquid shortening containing thenovel additive which is capable of producing excellent quality cakes.

Substantially all shortenings in general use today are glycerides in oneform or another. Although the naturally occurring liquid triglycerideoils have been used to some extent as shortening, they have in generalbeen found to be unsatisfactory for cake baking purposes in the absenceof the addition of various emulsifiers. It has been the more usualpractice to hydrogenate or harden liquid triglyceride oils with theresult that the plastic or solid shortenings are the most common typeavailable in the market today. These plastic shortenings usually arecombined with emulsifiers and other additives of various kinds toenhance the properties of the shortening and provide good cakeperformance in terms of volume, texture, and tenderness.

Because of the inconvenience of the plastic or solid shortening withrespect to handling, measuring, and mixing especially with other cakemaking ingredients it is desirable to use a liquid shortening. However,the emulsifiers that were so effective in the plastic shortening havebeen found to be deficient when used in a liquid shortening.

Various combinations of emulsifiers have been used in liquid shorteningsand some have been successful to a limited degree. While it is necessarythat the shortening composition, when used in cake baking, enhance cakebatter stability and produce a cake of greater volume, it is alsoimportant that the liquid be clear at about 60 F., be able to recoverits clarity at temperatures above 60 F. when the temperature of theliquid oil drops below about 60 F., be pourable at refrigeratortemperatures, and have a minimal smoking tendency at fryingtemperatures. The latter requirement is necessitated by the fact thatliquid oils are used by the consumer for functions other than as a cakemaking ingredient, e.g., frying. The prior art is replete with teachingsas to how to obtain these various requirements. For instance, U.S. Pats.3,293,272 and 3,370,- 958 disclose that half esters of succinic acidwith monoacylated propylene glycol find use as cake functionalemulsifiers at a weight level of at least 4% in a liquid oil such ascottonseed oil, soybean oil or peanut oil. These references state thatthe acyl radical, i.e. the fatty acid residue, should be substantiallycompletely hydrogenated. Unsaturated fatty acid residue such as oleicand linoleic acid residues are described as providing compounds that areineffective. However, some prior art emulsifiers have proven to beunsatisfactory, especially from the standpoint of producing liquidshortenings which maintain clarity after subjection to refrigeratortemperatures.

Accordingly, it is an object of the present invention to produce ashortening composition that is clear at temperatures above 60 F.,pourable at refrigerator temperatures, rapidly recovers its clarity whenremoved from refrigerator temperatures to temperatures above 60 F.,produces cakes that are of excellent quality and high volume, and thathas minimal smoking tendencies at frying temperatures.

It is a further object of this invention to produce a novel compoundhaving utility as a shortening additive.

It is a still further object of this invention to produce a shorteningcomposition containing a unique combination of emulsifiers.

These and other objects will become apparent from the description andexamples that follow hereinafter.

SUMMARY OF THE INVENTION A novel liquid oil additive, brassidoylpropylene glycol hydrogen succinate (BSPGHS) and the making of a novelliquid shortening composition is also produced by; (a) mixing with aliquid glyceride base oil form 0.8%-2.5% BSPGHS, from 1%-6% propyleneglycol fatty monoester with the ester group containing from 16 to 22carbon atoms and no more than 1.5% of the total composition containingpropylene glycol fatty monoester having an ester group containing 22carbon atoms, and from 0.2%-2.0% fatty monoand diglycerides containingfrom 14 to 22 carbon atoms, each by weight of the total composition; (b)desmoking the composition of (a) by steam stripping at a temperature of320 F. to 350 F. for from 30 minutes to 80 minutes; and (c) Winterizingthe desmoked solution at 50 F. to F. for from 1 hour to 12 hours.

DESCRIPTION OF THE INVENTION In general, the present invention comprisesthe making of a novel shortening additive, brassidoyl propylene glycolhydrogen succinate (BSPGHS) and the making of a novel shorteningcomposition containing a unique combination of emulsifiers.

The novel compound produced in accord with this invention and havingparticular utility as a liquid shortening additive is BSPGHS. BSPGHS isconviently made from the propylene glycol monoester of brassidic acid(PGMBS) by succination. PGMBS in turn is made from propylene glycol andbrassidic acid by direct esterification. In a typical example, brassidicacid was reacted with propylene glycol in a 1:10 molar ratio in 6 timestheir combined weight of xylene. The reaction was carried out in thepresence of a p-toluene sulfonic acid catalyst.

The reaction mixture was agitated mechanically for four hours whileheating at refluxing temperature. It was then cooled below 212 F. andwashed four times, each time with two times its volume of hot water. Theresultant mixture was then dried and mixed with succinic anhydride in a1:1.2 molar ratio. This reaction mix was refluxed for 6 hours at about280 F. The crude reaction product in xylene was then cooled to below 212F., water washed with two times its volume of hot water, and dried. Theproduct was obtained by adding sufiicient hexane to dissolve the residueand crystallizing it out of solution at 34 F. A second crystallizationfrom hexane at 34 F. produced the BSPGHS. It had a white, crystallineappearance and a melting point of about 53 C. Thin layer paperchromatography analysis revealed that the product was about 98% pureBSPGHS.

Alternatively the reaction between the propylene glycol monoester ofbrassidic acid and succinic anhydride can be carried out at temperaturesof from about 32 F. to about 160 F. in solvents such as chloroform,benzene, and ethyl acetate and in the presence of perchloric acidcatalyst. The isolation procedure is the same as above described. Insome cases the above described reactions can be carried out without thepresence of any solvent.

In accord with this invention it has been found that when the novelcompound BSPGHS is used in combination with certain known emulsifiers ina liquid triglyceride base oil there is obtained a unique liquidshortening composition possessing many deisrable properties. This novelliquid shortening, prior to desmoking and Winterizing as explainedhereinafter, comprises a liquid triglyceride base oil and as emulsifiersfrom 0.8% to 2.5% BSPGHS, from 1% to 6% propylene glycol fattymonoester, and from 0.2% to 2% fatty monoand diglycerides each by weightof the shortening. Additionally, up to 0.5% of behenoyl propylene glycolhydrogen succinate (BPGHS) can replace an equal weight amount of BSPGHS.The total emulsifier content of the shortening prior to desmoking andWinterizing amounts to 2% to 8% by weight. Lesser amounts fail to giveany noticeable emulsifier effect While emulsifier levels greater than 8%by Weight of the shortening adversely affect the taste and texture of acake containing the same. Preferably the shortening composition prior todesmoking and Winterizing comprises a liquid triglyceride base oil, from1% t 2% BSPGHS, from 1% to 5% propylene glycol fatty monoester, and from0.2% to 1% fatty monoand diglycerides with the total emulsifier contentbeing from 2.2% to 7%.

The base oil of the fluid shortening of this invention is a normallyliquid triglyceride. Suitable base oils of this shortening can bederived from animal, vegetable, or marine sources includingnaturally-occurring liquid triglyceride oils such as cottonseed oil,soybean oil, rapeseed oil, coconut oil, crambe oil, cambra oil,safilower oil, sesame seed oil, sunflower and sardine oil. Also suitableliquid oil fractions can be obtained from palm oil and lard, as forexample, by fractional crystallization or interesterification withsimultaneous crystallization of insoluble glycerides, followed byseparation of the liquid oil fraction. Oils predominating in glyceridesof unsaturated acids may require partial hydrogenation to maintainflavor. Refined cottonseed oil and refined and partially hydrogenatedsoybean oil (iodine value of about 110: 10) have been found to be verysuitable for use as glyceride base oils of this invention. Partiallyhydrogenated oils can be winterized to assure continued clarity.Preferably the base oils of this invention are desmoked by knownmethods, e.g., steam stripping prior to having added thereto the novelemulsifier system of this invention.

The propylene glycol fatty monoesters used in the above shorteningcomposition are well known compounds. The ester group contains 16 to 22carbon atoms with not more than 1.5% being monoester containing 22carbon atoms; greater amounts of C create clarity problems in theultimate product. Examples of this component found useful in thisinvention are propylene glycol monostearate, propylene glycolmonobrassidate, and propylene glycol monobehenate.

Fatty monoand diglycerides are also present in the shorteningcomposition for their emulsifier effect. These glycerides can be eitherpure esters of fatty acids having from 14 to 22 carbons, or mixtures offatty acid esters containing such fatty acids. They are convenientlyprepared by the superglycerination of fats or oils which consist ofreacting triglyceride fat or oil, for example, cottonseed or soybeanoil, with excess glycerine in the presence of an alkaline catalyst suchas sodium hydroxide. The ratio of monoto diglycerides of this additionis not important, the only concern being that a level of 0.2% to 2% ofeither monoglyceride, diglyceride, or a mixture be present.

BPGHS useful in this invention to replace up to 0.5% by weight ofshortening of the BSPGHS is a known compound. BPGHS is substitutedwhenever possible for the BSPGHS because of economic considerations.Slightly better cake making performance is also observed when limitedamounts of the BPGHS is substituted for the BSPGHS in the shortening ofthis invention. The reason for this phenomena is not known. The amountof BPGHS included in the shortening composition, however, must belimited to not above 0.5% because of the fact that higher levels impairthe clarity of the liquid shortening.

Additional minor ingredients can be added such as flavor, color,antioxidants, crystal modifiers and other known shortening additives.Examples of known additives that can be added to the novel shorteningcomposition of this invention are methyl silicone, butylatedhydroxytoluene, butylated hydroxyanisole, sorbic acid, and polysorbates.

The clear oil shortening is prepared by first dissolving all theemulsifier components in the liquid triglyceride base then desmoking thesolution by steam stripping. Steam stripping at a temperature rangingfrom 320 F. to 350 F. for from 30 minutes to minutes has the beneficialeffect of removing the components that impart organolepticallyobjectionable features to the shortening and also of improving thesmoking tendencies of the shortening composition, i.e. reducing thetendency of the shortening to smoke excessively at ordinary fryingtemperatures. For a description of steam stripping, see US. Pat. No.3,506,697. The steam stripped liquid oil is next winterized. Winterizingrefers to the known process whereby the shortening composition is firstcarefully cooled to a low temperature, i.e. for the purposes of thisinvention from 50 F. to 70 F. for 1 hour to 12 hours. This permitsprecipitation of solid high melting material that can then be separatedfrom the liquid oil to complete the winterization process. The resultantliquid oil is less susceptible to clouding when stored by the consumerfor extended times at low temperatures. It should be understood that thepurpose for Winterizing is to remove solid materials that precipitateout at low temperatures and are responsible for the cloudiness of aliquid oil and that this stepcan be eliminated if all of the componentsof the shortening composition of this invention are soluble at lowtemperatures, i.e., 60 F. and above.

The liquid oil made by the above process is clear at temperatures above60 F., recovers its clarity at 60 F. if cooled below this temperature,is pourable at refrigerator temperatures, and has minimal smokingtendencies.

The shortening of this invention is used in the prepara tion of alltypes of cakes, e.g. white, yellow, and chocolate cakes as Well as manyothers. Cakes containing the shortening of this invention in theirformulation possess excellent eating qualities and high cake bakingperformance. Generally from 8% to 20% of the instant shortening, from35% to 45% sugar, and from 30% to 45% flour on a dry ingredient weightbasis are used in the EXAMPLE I.FORMULATION Percent BSPGHS 1.4 Propyleneglycol monostearate 2.6 Propylene glycol monobrassidate 1.0 Propyleneglycol monobehenate 0.3 Mono-diglyceride of palm oil 1.0 Behenic acid0.2

Soybean oil,

odorized) 93.500

After all of the additives are dissolved in the oil the product isdesmoked by passing steam at 325 F. through the product for about 60minutes. The resultant product is next winterized to remove the highermelting components of the emulsifiers by cooling the desmoked product to60 F. and holding it at that temperature for about 3 hours. Thissolution is next filtered to give a clear oil shortening product that isclear at 60 E, pourable at refrigerator temperatures, and recovers itsclarity when removed from refrigerator temperatures to temperaturesabove 60 F. The product also has a smoke point about 20 F. lower thanthe smoke point of a leading commercially available all-purposeshortening. The quality of cakes made using this unique shorteningcomposition can be seen by the following example.

-IV=107 (winterized and de- (Mix for 2 min. on a conventional householdmixer at 500 r.p.m.) Add:

Fresh egg white 60 Whole milk 40 (Mix additional 2 min. at 500 r.p.m.)

Scale 8-inch pans at 400 g. batter Baking temperature, 365 F. Bakingtime, 25 min.

The resultant cakes have high volumes and possess excellent eatingqualities.

6 When 0.5% BPGHS replaces an equal amount of BSPGHS in the formation ofExample I, the shortening prepared therefrom shows slightly better cakemaking performance qualities than the shortening of Example I. 5 What isclaimed is:

1. A method of making a liquid shortening composition, which comprises:

(a) forming a composition containing a liquid triglyceride base oil andas emulsifiers from 0.8% to 2.5% brassidoyl propylene glycol hydrogensuccinate, from to 0.5% of behenoyl propylene glycol hydrogen succinateand when more than 0% said compound replacing an equal amount ofbrassidoyl propylene glycol hydrogen succinate, from 1% to 6% propyleneglycol fatty monoester with the ester group containing 16 to 22 carbonatoms and from 0.2% to 2% fatty monoand diglycerides with the monoanddiglyceride ester group containing 14 to 22 carbon atoms, each by weightof the total composition said composition containing no more than 1.5 byweight of propylene glycol fatty monoester having an ester groupcontaining 22 carbon atoms;

(b) desmoking the composition of (a) by steam stripping at a temperaturefrom 320 F. to 350 F. for from 30 minutes to 80 minutes; and

(c) Winterizing the desmoked composition at from 50 F. to 70 F.

2. The method of claim 1 wherein the emulsifier content prior todesmoking is 2% to 8% by weight of the total composition.

3. The method of claim 2 wherein the desmoked composition is winterizedfrom 1 hour to 12 hours.

4. The method of claim 3 wherein the liquid triglyceride base oil issoybean oil having an iodine value of about 1101-10.

5. The method of claim 3 wherein the liquid triglyceride base oil iscottonseed oil having an iodine value of about 110: 10.

6. The method of claim 1 wherein the composition prior to desmokingcomprises from 1% to 2% of the brassidoyl propylene glycol hydrogensuccinate, from 1% to 5% of the propylene glycol fatty monoester andfrom 0.2% to 1% of the fatty monoand diglycerides.

7. The method of claim 6 wherein the total emulsifier content prior todesmoking is from 2.2% to 7% by weight of the total composition.

8. The liquid shortening composition produced by the method of claim 1.

References Cited UNITED STATES PATENTS 3,293,272 12/1966 Freund 99-123 X3,370,958 2/ 1968 Freund 99-118 R X 3,402,050 9/1968 Howard et a1 99118R JOSEPH M. GOLIAN, Primary Examiner US. Cl. X.R.

